WPWR-TV sold its spectrum space in the Federal Communications Commission (FCC)'s incentive auction,[2] and began channel-sharing with WFLD on June 11, 2018.

A large percentage of WPWR's programming schedule was occupied by SportsVision, a new pay television service which Eychaner had developed through a deal with Chicago White Sox co-owners Jerry Reinsdorf and Eddie Einhorn.

To receive the service, viewers had to rent a set-top converter and pay a monthly fee in order to view SportsVision's event telecasts, involving the Chicago sports teams.

The FNN simulcast was dropped in January 1984, at which time the station added several classic sitcoms from the early to mid-1950s and older cartoons to its schedule.

One of the notable events for WBBS occurred in 1983, when the station introduced the Latin teen pop group Menudo (which included a young Ricky Martin) to Chicago's Latino community.

[3] When it applied for the station in 1979, GWWX-TV had proposed part-time subscription television operation, as well as news and information for the African American community.

The license had been transferred to Northwest Indiana Public Broadcasting, which was attempting to raise funds to rebuild channel 50 from a newer, more centrally located facility in the region.

The FCC approved such swaps among channels in the same band, as was the case with the two UHF stations, in March 1986,[6] and in August, the commission issued final orders switching the commercial and noncommercial allocations for Gary.

[7] The money Northwest Indiana Public Broadcasting received from Metrowest enabled it to land a federal grant to build out its facility, which returned to the air November 15, 1987, as WYIN.

WBBS-TV owner Miyares, realizing that the loss of the NetSpan affiliation would be crippling for his station, reduced WBBS' programming schedule to 8 p.m. to its late-night sign-off on weekend evenings late that year, selling the rest of the weekday time periods that his station had occupied to Eychaner, allowing WPWR to broadcast full-time on weekdays.

Representatives for The CW were on record as preferring to align with UPN and The WB's "strongest" affiliates; WGN-TV had been well ahead of WPWR in the ratings since the latter's sign-on.

[28][29] However, in negotiating the terms of the deal, Tribune decided not to renew The CW's affiliation with WGN-TV after the expiration of their initial ten-year agreement on September 1, 2016.

Tribune decided to run WGN-TV as an independent, allowing it to fully commit to its schedule of local sports without the requirements to move some broadcasts to WPWR-TV due to network limits on preemptions, and to rebroadcast preempted programming on The CW's off nights.

On July 11, 2016, WPWR-TV unveiled its CW-standardized logo with the launch of a "Make the CWitch" promotional video advertising the then-pending switch.

With The CW's move, the MyNetworkTV programming returned to prime time on WPWR's weeknight schedule, airing from 8 to 10 p.m., sandwiched between episodes of Chicago P.D.

(carrying four episodes of the series from the programming service and syndication on Tuesday evenings); the loss of the CW affiliation led the station to return to the "My50 Chicago" branding on September 1, 2019.

Occasionally as time permits, WPWR may air Fox network programs whenever WFLD is unable to in the event of extended breaking news or severe weather coverage.

WPWR is the only major television station in the Chicago market that has never aired regularly scheduled local news programming of any kind.

[40] The 30-minute program covers one to two cases per episode and features interviews with detectives and family members, as well as walk-throughs of the actual crime scenes and dramatic reenactments.

[41] In October 2017, Case Files Chicago was nominated for an Emmy Award by the National Academy of Television Arts and Sciences Chicago/Midwest Chapter in "Outstanding Achievement for Public Affairs/Current Affairs Programming – Series" for their season 5 episode profiling the unsolved murder of Anthony "TJ" Green.

Starting with the 2008 season, WPWR obtained broadcast rights to games from the Major League Soccer franchise Chicago Fire S.C.

[47][48][49] Through an agreement with Tribune Broadcasting, WPWR became a tertiary outlet for the Chicago Cubs and Chicago White Sox beginning in the 2015 season, broadcasting occasional telecasts of the two teams' Major League Baseball games that are produced by WGN-TV (through its WGN Sports programming unit), due to that station's network affiliation contracts with The CW that limit the number of programming preemptions that WGN-TV is allowed on an annual basis (these telecasts were previously seen on WCIU-TV, which discontinued its overflow agreement with WGN as a result of the January 12, 2015, launch of a prime time newscast produced by ABC owned-and-operated station WLS-TV, channel 7).